Vinyl ether-phosgene interpolymer-ization products and process of producing the same



Patented Mar. 15, 1949 UNITED STATES lZATENT 0 FFICE VINYL ETHER-PHOSGENE IZATION PRODUCTS PRODUCING THE SAM Frederick Grosser, Easton,

INTERPOLYMER- IEAND PROCESS OF Pa., assignor to General Aniline & Film Corporation. New York, N. Y., a corporation of Delaware No Drawing. Application November 29, 1945, Serial No. 631,779

6 Claims. (Cl. 260-90) The present invention relates to novel intergene having a molar "temperature of 45 to 50 C. for 23 hours. There As ethylenically-unsaturated ethers which are 1 suitable for use in the present invention, may be cited those ethers having the formula R;O -CR =CRFR in which R, R R and R aryl, or aralkyl alcohols stand for an alkyl, aryl or aralkyl group and R, R or R also may.

While neither the vinyl ethers nor phcsgene is readily polymerized under the conditions employed for producing these novel interpolymers, I have found that a mixture of an ethylenicallyunsaturated ether and phosgene may readily be polymerizedby slightly heating the same, preferably in a closed system. The exact temperature of heating is not highly critical and it may be varied through a relatively wide range. In general, temperatures of from to 60 C. are satisfactory and permit the polymerization to be carried out in a reasonable time with a good yield of polymeric material. Likewise, the relative proportions of the ethylenically-unsaturated ether and phosgene are not highly critical and may be varied through a relatively wide range. Satisfactory interpolymers have been prepared when the relative proportions of ethylenicallyunsaturated ether and phosgene were varied within the range of 1:1 to 10:1. If desired, the polymerization may be carried out in the presence of inert organic solvents, such as chloroform. benzene. toluene, petroleum naphtha and the like.

2 The following specific examples illustrate preferred embodiments of the present invention:

Example 1 A mixture of isopropyl vinyl ether and phosratio of 3:1 was heated to a was obtained 76% of a soft brown tacky solid resin which was insoluble in benzene, acetone, chloroform and other common organic solvents.

Example 2 A mixture of isopropyl vinyl ether and phos gene having a molar ratio of 7.5:1 was heated to 45 to C. for 40 hours. There was obtained 69% of a dark brown, rubbery solid resin which was insoluble in common organic solvents.

Example 3 A mixture of .75 moles of isopropyl vinyl ether, 0.1 mole'of phosgene and 1 mole of chloroform was heated to 45 to50 C. for 18 hours. There was obtained of a black, rubbery, non-tacky solid resin which was insoluble in common oranic solvents.

I claim:

l. A method of polymerization which comprises slightly heating a mixture of phosgene with an ethylenically-unsaturated ether having the in which R stands for a member of the group consisting of alkyl, aryl and aralkyl radicals and R stands for a'member of the group consisting of hydrogen and alkyl, aryl and aralkyl radicals, the molar ratio of said ether to said phosgene-being within the range of 1:1 to 10:

2. The interpolymerization products obtained in accordance with claim 1.

3. A method of polymerization which comprises heating to a temperature of 40-80 C. a mixture of a vinyl ether of an aliphatic alcohol and phosgene in molar proportions 01 1:1 to 10:1.

4. The interpolymerizatlon products obtained in accordance with claim 3. I

5.41 method of polymerization which comprises heating to a temperature of 40-60 C. a mixture of isopropyl vinyl ether and phosgene in molar proportions of 1:1 to 10:1.

6. The interpolymerization products obtained in accordance with claim 5.

FREDERICK GROSSER.

No references cited.

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